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2) Citronellal, a chiral pool reagent, can be transformed into menthol in a 2 step sequence with another natural product as a synthetic intermediate. Provide the missing intermediate, identify it, provide the mechanism for its formation, and provide a clear, 3D representation that leads to the observed stereochemical outcome in this reaction. Me H Me ZnBr2 H2. Pd/C Me Me Me Me
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